Place the cherries, sugar, and 2 tablespoons water in a large saucepan. Bring the mixture to a boil, then reduce heat and simmer, stirring often, until the cherries break down and the liquid turns to a thick syrup, 10 to 12 minutes. Transfer to a bowl and refrigerate until cool, about 15 minutes.

Using an electric mixer, beat the cream, condensed milk, and vanilla in a large bowl on medium-high until stiff peaks form, 3 to 4 minutes. Gently fold in the chocolate chunks.

Spoon half the cream mixture into a 4 1/2- by 8 1/2-inch loaf pan or 1 1/2-quart freezer-safe container. Spoon half the cherry mixture on top. Using a knife, swirl the cherry mixture through the cream. Repeat with the remaining cream and cherry mixture. Freeze until set, at least 4 hours. Once set, cover with plastic wrap and freeze for up to 2 weeks.

Tips & Techniques

Easy Upgrade: Make store-bought cones special by dipping the outside in melted chocolate. Let dry for 20 seconds before coating in chopped nuts, sprinkles, or shredded coconut.

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